ALT How do interest groups learn about and influence politicians over time? We develop a game-theoretic model where an interest group can lobby a politician while learning about their ideological alignment. Our analysis reveals a fundamental tradeoff: interest groups must balance gathering information against exerting immediate influence, while politicians strategically manage their reputations to shape future interactions. These strategic forces generate systematic dynamics: policies and transfers shift in tandem, with early-career politicians showing greater policy variance and extracting larger rents through reputation management than veterans. Uncertainty about alignment increases policy volatility as groups experiment with offers, while institutional features like committee power and revolving-door incentives systematically alter both learning incentives and influence strategies. Our results shed new light on how interest group influence evolves across political careers and ...